The Best Deal I Ever Made…

…had absolutely nothing to do with real estate.

I was sitting at the dining room table, talking with my two older boys, 10 & 12.

Like a lot of kids that age, they wanted to make their own money. Their options were limited, but they landed on a timeless first hustle: mowing lawns.

Now, we live in the South, where summer feels like living in a steam room — 95 degrees and 90% humidity on a good day. Lawn care is always in demand.

They pooled $400 of their saved allowances to buy a solid Honda push mower and got to work. I let them borrow my old Ryobi weed eater to round out their setup, and they started cutting grass for our yard, their grandparents, and some family friends.

Business was good — so good, in fact, they quickly made back their initial investment. But there was one problem: that old Ryobi weed eater was a disaster.

It was stubborn to start, and William, my 12-year-old, wrestled with it constantly. Every time I drove them to a job and sat in the car working, I’d inevitably have to get out to help restart the thing.

By the end of their first week, it was clear this wasn’t sustainable. I sat them down and said, “If you guys are serious about this, you need better equipment.”

They agreed, but there was a snag. They’d spent their startup capital on the mower and only had $100 made from their first round of jobs. A good weed eater cost $379.99, which left them short.

This was my chance to teach them a bigger lesson about business.

“You need an investor,” I told them.

Now, I could’ve just lent them the money myself. That would’ve been the easy route. But then I had an idea.

My cousin and business partner, Jennings, had been teaching his son, Jennings Jr., about saving and investing. He’d been doing odd jobs and saving his birthday money, so I figured this could be a perfect opportunity for all the kids to learn.

I helped William and Phineas put together a pitch deck. Yes, a real pitch deck — with slides on their business model, current earnings, and how they planned to pay back the loan. Then I called Jennings.

“Hey,” I said, “the boys are starting a lawn care business, and they need to pitch an investment opportunity. They want to pitch it to your Jennings Jr. What do you think?”

Jennings was all in.

We all got together in the office so William & Phineas could pitch to Jennings Jr.

I could see the nervousness bouncing around the room.

Because of course…it’s a 12yr old and 10yr old talking to an 8yr old about investing $300 with them.

When I was 8…$300 was a FORTUNE!

And they crushed it. They broke down how much they needed, how they’d repay it, and what kind of return on investment he could expect. Even what colateral they had for the loan.

The AAR was pretty high, by the way…hard money type personal loan…*smile*

The boys sealed the deal with Little Jennings, complete with promissory notes and everything. They bought the new weed eater, finished out the summer cutting grass, and worked hard to pay back their loan.

They learned how to manage debt, track expenses, even how to raise capital for their little start up operation!

That deal wasn’t just about lawn care. Or making returns on capital.

It was about entrepreneurship, financial literacy, and learning the power of teamwork and creativity.

Easy to see why the best deal I ever did wasn’t in real estate.

It was connecting three boys to help them take another step toward a dream.